5-Hydroxyindoleacetic Acid → 2-(5-hydroxy-1H-indol-3-yl)-N-[2-phenyl-1-(3-phenyltriazol-4-yl)ethyl]acetamide

HRID 1506635

반응식

HRID 1506635 반응식
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[NH:31][CH:30]=[C:29]2[CH2:35][C:36]([OH:38])=O.CCN(C(C)C)C(C)C.[C:48]1([CH2:54][CH:55]([C:57]2[N:61]([C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=3)[N:60]=[N:59][CH:58]=2)[NH2:56])[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CN(C=O)C>[OH:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[NH:31][CH:30]=[C:29]2[CH2:35][C:36]([NH:56][CH:55]([C:57]1[N:61]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)[N:60]=[N:59][CH:58]=1)[CH2:54][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)=[O:38]

참가 물질

6

반응물 4

HCID 18265-Hydroxyindoleacetic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 902812472-phenyl-1-(1-phenyl-1H-1,2,3-triazol-5-yl)ethanamine

생성물 1

HCID 902812762-(5-hydroxy-1H-indol-3-yl)-N-[2-phenyl-1-(3-phenyltriazol-4-yl)ethyl]acetamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

HATU (40 mg, 0.105 mmol) was added to a solution of 2-(5-hydroxy-1H-indol-3-yl)acetic acid (19.2 mg, 0.1 mmol) and DIPEA (0.02 mL, 0.12 mmol) in DMF (0.3 mL). After 10 minutes, 9D (26.5 mg, 0.1 mmol) in 0.2 mL of DMF was added to the reaction. The reaction was stirred for 2 hours. LC/MS shows desired product with a small amount of acid. Purified reaction mixture on prep reverse phase HPLC using 20-80% B over 20 min. (A=0.1% TFA/H2O; B=0.1% TFA/Acetonitrile). Combined pure fractions as determined by LC/MS and lyophilized to provide the desired product. 1H NMR (400 MHz, CD3OD) δ 7.76 (s, 1H), 7.47 (t, J=7.5 Hz, 1H), 7.39 (t, J=7.6 Hz, 2H), 7.21-7.01 (m, 6H), 6.96 (s, 1H), 6.84 (d, J=1.9 Hz, 1H), 6.78 (d, J=6.8 Hz, 2H), 6.68 (dd, J=8.6, 2.3 Hz, 1H), 5.46 (s, 2H), 5.21 (t, J=7.6 Hz, 1H), 2.96 (ddd, J=21.5, 13.3, 7.6 Hz, 2H); MS (m/z) 438 [M+H]+.

출처 및 근거

ORD 기록
ord-b9a3c52a6e754d8fb0397816574848a6
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09220710B2

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